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Alyssa Milano and Brad Penney

Alyssa Milano and Brad Penny

Before Milano, who had a handful of hit pop albums in Japan, was designing a line of baseball-inspired fashions, dubbed Touch, she was getting an intimate look at the sport courtesy of boyfriend Brad Penny. The pair have since split up, but Milano has been associated in the tabloids with a host of baseball stars, including pitcher Carl Pavano and catcher Russell Martin.

(OK, so perhaps it's a stretch counting Milano as a pop singer here, but we needed 10 slides. And here's proof.)